Ethylene → 7-Bromo-2-tetralone

HRID 656379Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH2:12]=[CH2:13]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:12][CH2:13][C:9](=[O:11])[CH2:8]2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6325Ethylene

HCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 36915747-Bromo-2-tetralone

Procedure

Scheme 3 illustrates a route to 7-substituted tetralin derivatives 10 and 11. 3-Bromophenylacetic acid is converted to the corresponding acid chloride and this is subjected to Friedel-Crafts reaction with ethene, affording the 7-bromo-2-tetralone 9. This intermediate may be elaborated using the procedures described in Scheme 1 to provide the acid 10 and aniline 11.

Sources & evidence

ORD record: ord-c3d06b89b54b4603806ffd1451d82fa8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071771B2

Reaction notes

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